Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis

Sandrine Ventre, Filip R. Petronijevic, David W.C. Macmillan

Research output: Contribution to journalArticle

211 Scopus citations

Abstract

The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

Original languageEnglish (US)
Pages (from-to)5654-5657
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number17
DOIs
StatePublished - May 6 2015

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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